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How to go from structureless to structured without losing your vibe

Lessons on creating an engineering ladder

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Moving Towards Structure 
Camille Fournier 
CTO, Rent the Runway 
@skamille
My Story 
• Grew Rent the Runway’s engineering team 
from ~12 to 55 and counting
My Organizational Goals 
• To create a relatively meritocratic 
environment 
• To limit bias 
• To develop the leadership talent on my team 
• To hire a diverse workforce
Flat 
• We start flat, except of course for “the 
founders” or perhaps “the executives” 
• First you have 3 directs 
• Then 5 
• Then 10 
• Then… you start to break down
Time to add some structure! 
• Maybe I’ll hire a VP of Engineering!
How about a Tech Lead? 
• Great I’ll take my most senior/favorite dev and 
make them “Tech Lead” of some of the 
software

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How to go from structureless to structured without losing your vibe

  • 1. Moving Towards Structure Camille Fournier CTO, Rent the Runway @skamille
  • 2. My Story • Grew Rent the Runway’s engineering team from ~12 to 55 and counting
  • 3. My Organizational Goals • To create a relatively meritocratic environment • To limit bias • To develop the leadership talent on my team • To hire a diverse workforce
  • 4. Flat • We start flat, except of course for “the founders” or perhaps “the executives” • First you have 3 directs • Then 5 • Then 10 • Then… you start to break down
  • 5. Time to add some structure! • Maybe I’ll hire a VP of Engineering!
  • 6. How about a Tech Lead? • Great I’ll take my most senior/favorite dev and make them “Tech Lead” of some of the software
  • 7. Perhaps a Director of Engineering • Not quite VP, not quite Tech Lead
  • 8. Either way, your flat is dead • It was never true anyway, so it’s probably for the best
  • 9. What does this new leader DO? • They make my life easier, of course!
  • 10. No, really • I dunno. They handle… – Project Management! – People Management for part of the team! – All Management so I don’t have to! – Architecture!
  • 11. If you don’t know, you’re set up to fail • Inevitably, this person is going to not read your mind exactly the way you wish they did • How do you know whether they’re incompetent or just confused? • How do you hold them accountable when you don’t know what they’re SUPPOSED to be doing?
  • 12. “They’ll define the role themselves!” • If you hire someone who has done this job before and you have a shared context, that might be ok – IE, you both worked for Google, and you hired a senior manager at Google to be a Director of Engineering
  • 13. A bad, but common, case • HR hires people with random titles based on what you said you needed to hire • “Frontend Engineer” • “Lead DevOps” • “iOS Specialist” • Pay people directly based on experience and whatever HR magic formula
  • 14. Creating Clarity The minute you create hierarchy, you need clarity
  • 15. The Engineer Ladder: What • The list of job levels and the description of what goes in each of those levels • BEST PRACTICE: Above Senior Engineer, has a separate path for “Manager” vs “Individual Contributor” • A device to create clarity on your team and, if done well, limit bias
  • 16. The Engineering Ladder: Why • Gives you a framework for hiring, paying, promoting • Forces you to become more clear in what you expect from people • Forces you to push that clarity into your hiring process and possibly hire better • Gives your team a growth path that helps them imagine their future with you
  • 17. Creating an Engineering Ladder • Step 1: Ask your friends for theirs – Step 0: Make friends with people who have teams big enough to justify a ladder • Step 2: Be realistic about how it applies to your team – You may not need all the levels. You may need more levels. • Write it up. Get feedback. Rewrite it. • Share it.
  • 18. I really don’t want to do this Why not?
  • 19. I’m afraid everyone will be clamoring for titles • They probably will when you roll this out BUT • This gives you the chance to make it clear to them what success looks like! • Give them something to work towards! • Give you both a framework for talking about how they are succeeding and how they are not
  • 20. Expect some anxiety • Ladder rollouts do generate anxiety around upward mobility • On the flip side, with no ladder, people that care about upward mobility leave for a better title elsewhere
  • 21. I’m afraid people will think they should be promoted who aren’t ready • Well then, that is why you need to be very clear about what you expect at each level • People will want to be promoted with or without a ladder, if you have any sort of leadership • They’ll also want bigger pay, more options, bigger projects • How do you determine who gets what?
  • 22. I’m afraid titles will cause us to lose voices of others • It takes more than “no titles” to ensure that voices are actually heard
  • 23. There are more paths to excellence than climbing a ladder! • True! And a ladder doesn’t take the place of other training • Embrace add-ons, badges, specialties
  • 24. Premature optimization! • True. You probably don’t need to do this when you have only 1 non-founder/executive “leader” • But the minute you need 2…
  • 25. Your vibe is a function of your company values and culture Do you know what your company values are? It is very possible to design a ladder to reflect and reward those values WHAT ABOUT MY VIBE?
  • 26. I’m the CTO, this isn’t my job! • Like hell it isn’t • If you are very lucky, you might find a VPE to do this for you – I would not hold my breath • This isn’t rocket science. If you can architect a system, you can architect a team.
  • 27. Conclusion • Clarity Clarity Clarity • Clarity